He continues to deny he lives there, lied to the police when they came with a code violation and inspection, and most recently overloaded the electrical and blew/snapped the line! 

Another downside is you loose on the advantages, of the Federal Tax Code, by not closing in the name of a LLC (you can elect to have a LLC taxed, as a S Corporation which is a whole other conversation).If you want to close in the name of a LLC, Mortgage Lenders will offer you Commercial Loan Terms (25-30% down, a 15-25 year amortization, and a ballon due in 5-7 years).

I think are benefits/drawbacks to both scenarios. 

The bank will make you leave 25% equity in the property - but you also still want the property to at least cash flow some - so be careful how much equity you pull out / new debt you take on.I would do a cost benefit analysis of what your actual gain is in cash-flow on buying a new property with a (currently) higher interest rate (if financing), versus just holding on to the current appreciated property and enjoying that cash flow.All the best!

It will familiarize you with the basic terminology and benefits.

I didn't get the benefit of hanging around guys who knew anything, the press guys were all blue collar stiffs that were going paycheck to paycheck and my father was making sales calls while I was in school so it was pretty rare I got to see those.

A benefit of this setup is that VRBO still processes payments and handles the transaction.

Benefit of waiting is lower mortgage payments and lower debt.

There are plenty of STR-savvy CPAs who can help you navigate the rules, maximize tax benefits, and make sure everything is done right.

I just do not understand the need to add "benefits" to the programs  that are just not real.